Skip to main content

The best vacation rentals in Islamorada

Check out our selection of great vacation rentals in Islamorada

Filter by:

Review score

See the latest prices and deals by choosing your dates.
Anglers Reef Paradise, hotel in Islamorada

Anglers Reef Paradise is located in Islamorada, 984 feet from Windley Key, and a private beach area, free bikes and an outdoor swimming pool are accessible in-house. This property offers free WiFi.

It was very clean and confortable; and the facilities where great, we enjoyed our time at the beach and used the canoes and paddle board! Great time
Scored 9.3
9.3
Rated wonderful
Wonderful
23 reviews
Anglers Reef Getaway, hotel in Islamorada

Offering an outdoor swimming pool and a garden, Anglers Reef Getaway in Islamorada is close to Windley Key and Windley Key Fossil Reef Geological State Park.

Walking distance to pool and around neighborhood!
Scored 9.1
9.1
Rated wonderful
Wonderful
23 reviews
Matecumbe Resort, hotel in Islamorada

Matecumbe Resort features a public bath and air-conditioned accommodations in Islamorada, 1.2 miles from Sea Oats Beach.

The property is nice! I just think it could very well be more taken care of! Found a dead rat on the way of the childrens park, the beach is wasnt so nice…
Scored 8.6
8.6
Rated excellent
Excellent
330 reviews
Topsider Resort by Capital Vacations, hotel in Islamorada

A 7-minute walk from Sea Oats Beach in Lower Matecumbe Beach, Topsider Resort by Capital Vacations offers accommodations with access to a hot tub.

Good location and spacious rooms. Close to water.
Scored 9.0
9.0
Rated wonderful
Wonderful
13 reviews
Welcome to the Pelican Lodge !, hotel in Islamorada

Welcome to the Pelican Lodge! is a recently renovated apartment in Tavernier where guests can make the most of the private beach area and tennis court.

It was clean, had everything we needed for a comfy stay, and was easy to get to.
Scored 9.2
9.2
Rated wonderful
Wonderful
21 reviews
Fiesta Key RV Resort Waterfront Cottage 33, hotel in Islamorada

Located in Layton in the region of Florida, this family and is 28 miles from Key Largo. The property features views of the sea and is 21 miles from Marathon.

Location is still the same
Scored 8.6
8.6
Rated excellent
Excellent
58 reviews
Fiesta Key RV Resort Premium Room 3, hotel in Islamorada

Fiesta Key RV Resort Premium Room 3 is located in Layton, just 15 miles from Windley Key and 17 miles from Florida Keys Aquarium Encounters.

Everything
Scored 8.0
8.0
Rated very good
Very Good
22 reviews
Fiesta Key RV Resort Standard Room 8, hotel in Islamorada

Featuring an outdoor pool, Fiesta Key RV Resort 15 is a villa located in Layton. The air-conditioned unit is 27 mi from Key Largo. There is a flat-screen TV and a private bathroom with a bath.

restaurant
Scored 8.3
8.3
Rated very good
Very Good
77 reviews
Ocean Pointe Suites at Key Largo, hotel in Islamorada

Set in the Florida Keys in the city of Tavernier, this all-suite property features in-room fully equipped kitchens and easy access to Key Largo, 10 minutes' drive away.

Place is convenient and good location
Scored 7.9
7.9
Rated good
Good
1,935 reviews
Coconut Bay Resort - Key Largo, hotel in Islamorada

Guests at this Key Largo resort can venture into the Gulf of Mexico on a kayak or paddle boat, swim in the heated outdoor pool, or stay in and read email through free Wi-Fi.

Beautiful tropical grounds. Waterfront access to gorgeous sunsets and water sports with provided kayaks and SUP. Super friendly staff and delicious complimentary morning coffee and scones from Peg.
Scored 9.2
9.2
Rated wonderful
Wonderful
114 reviews
All vacation rentals in Islamorada

Most booked vacation rentals in Islamorada this month

Enjoy breakfast in Islamorada!

  • Anglers Reef Getaway
    Scored 9.1
    9.1
    Rated wonderful
    Wonderful
     · 23 reviews

    Offering an outdoor swimming pool and a garden, Anglers Reef Getaway in Islamorada is close to Windley Key and Windley Key Fossil Reef Geological State Park.

    The location was close to the water & other amenities

  • Anglers Reef Paradise
    Scored 9.3
    9.3
    Rated wonderful
    Wonderful
     · 23 reviews

    Anglers Reef Paradise is located in Islamorada, 984 feet from Windley Key, and a private beach area, free bikes and an outdoor swimming pool are accessible in-house. This property offers free WiFi.

    Location & the grounds & pool were amazing.

  • Matecumbe Resort
    Scored 8.6
    8.6
    Rated excellent
    Excellent
     · 330 reviews

    Matecumbe Resort features a public bath and air-conditioned accommodations in Islamorada, 1.2 miles from Sea Oats Beach.

    El lugar es súper bonito! Y es Perfecto para la familia

  • Tollgate Tides
    Breakfast options

    Just a 6-minute walk from Anne's Beach and one mile from Sea Oats Beach, Tollgate Tides features accommodations in Islamorada with a garden.

  • Beachfront Villa at Islamorada BY THE GLAMHOMES

    Providing an outdoor swimming pool, Beachfront Villa at Islamorada BY THE GLAMHOMES offers accommodations in Islamorada.

  • Plaza Del Sol
    Breakfast options

    Plaza Del Sol is located in Islamorada, just 1.4 miles from Anne's Beach and 8.2 miles from Upper Matecumbe Key. This vacation home features accommodations with a balcony.

  • Two White Turtles

    Two White Turtles offers accommodations in Islamorada, 21 miles from Florida Keys Aquarium Encounters and 21 miles from Pigeon Key.

  • Key Lime Cottage in the heart of Islamorada
    Scored 8.0
    8.0
    Rated very good
    Very Good
     · 1 review

    Key Lime Cottage in the heart of Islamorada is located in Islamorada, just 1.6 miles from Sea Oats Beach and 5.3 miles from Upper Matecumbe Key.

These vacation rentals in Islamorada have options with FREE cancellation

  • Waterfront Wonder
    Free cancellation options available

    Waterfront Wonder is located in Islamorada, just 1.5 miles from Anne's Beach and 7.6 miles from Upper Matecumbe Key. Guests may go for a swim in the private pool.

  • Casa Koto
    Free cancellation options available

    Casa Koto offers accommodations in Islamorada, a 13-minute walk from Sea Oats Beach and 1.4 miles from Anne's Beach. This beachfront property offers access to a balcony and free Wifi.

  • Sun-kissed Bliss
    Free cancellation options available

    Sun-kissed Bliss offers accommodations in Islamorada, 21 miles from Pigeon Key and 22 miles from Florida Keys Aquarium Encounters.

  • EXECUTIVE BAY ISLAMORADA BY SOFLA VACATIONS
    Scored 8.5
    8.5
    Rated very good
    Very Good
     · 2 reviews

    EXECUTIVE BAY ISLAMORADA BY SOFLA VACATIONS in Islamorada provides accommodations with a private beach area, an outdoor swimming pool, and a garden.

  • Paradise Beach
    Free cancellation options available

    Paradise Beach offers accommodations in Islamorada, a few steps from Sea Oats Beach and 1.2 miles from Anne's Beach. This beachfront property offers access to free Wifi.

FAQ about vacation rentals in Islamorada

Vacation Rentals That Guests Love in Islamorada

  • Avg. price/night: $215.08
    Scored 7.1
    7.1
    Rated good
    Good
     · 1,111 reviews
    I loved the property I come out here every year and it never disappoints! The pool villas are my favorite to stay at
    leon
    Young couple
  • Avg. price/night: $324.23
    Scored 8.3
    8.3
    Rated very good
    Very Good
     · 248 reviews
    We had a great time at Bayside Villas. The townhome was clean and comfortable. The pool and boat slips were close and convenient. We really enjoyed having access to the resort. We enjoyed the pool, poolside restaurant and all the amenities there. We also loved being able to contact the shuttle for rides to and from the resort and local restaurants. We thoroughly enjoyed our stay and look forward to visiting again later this summer.
    Michael
    Family with young children
  • Avg. price/night: $324.23
    Scored 8.3
    8.3
    Rated very good
    Very Good
     · 248 reviews
    The villa was clean and very nice. The location is quiet. Parking close to the door was great. Housekeeping does a great job.
    Tate
    Young couple
  • Avg. price/night: $268.87
    Scored 7.8
    7.8
    Rated good
    Good
     · 1,056 reviews
    Beautiful property, great location, free breakfast, wonderful villa view, very friendly staff, most comfortable beds, loved the shower.
    Janelle
    Young couple
  • Avg. price/night: $324.23
    Scored 8.3
    8.3
    Rated very good
    Very Good
     · 248 reviews
    The location of the property. Close to great restaurants. The basketball by the beach was phenomenal, ping pong and activities were great. The pools were great and the view of sunset by the villas pool was fantastic.Beautiful property. We will return.
    Maurizio
    Family with young children
  • Avg. price/night: $248.63
    Scored 8.0
    8.0
    Rated very good
    Very Good
     · 443 reviews
    We didn't get the villa on the beach that we paid for, but they did upgrade us to what was probably a more comfortable 2 BR, 2 bath small house.
    Norm
    Family with young children
  • Avg. price/night: $302.79
    Scored 8.6
    8.6
    Rated excellent
    Excellent
     · 1,598 reviews
    Last year we stayed there and it was great, location, resort, staff and weather. This year was meh. Service at the poolside restaurant was spotty. They renamed the villages causing confusion so this year is was meh.
    Ron Moz Sr
    Young couple
  • Avg. price/night: $280.13
    Scored 8.0
    8.0
    Rated very good
    Very Good
     · 862 reviews
    Villa was lovely, spacious and comfortable! Great location overlooking the sea.
    Yasmina123
    Young couple
  • Avg. price/night: $324.23
    Scored 8.3
    8.3
    Rated very good
    Very Good
     · 248 reviews
    The villas were spacious and clean
    W
    William
    Family with young children
  • Avg. price/night: $280.13
    Scored 8.0
    8.0
    Rated very good
    Very Good
     · 862 reviews
    The layout and I like that’s acomplete boutique hotel unique great staff and absolutely great planned villas n rooms
    ventura
    Family with young children